CN1103764C - Substituted phenyl uracils - Google Patents

Abstract

New substituted phenyl uracils are described which have general formula (I), whereby R<1> is hydrogen, halogen or optionally substituted alkyl, R<2> is optionally substituted alkyl, R<3> is hydrogen, an amino group or optionally substituted alkyl, alkenyl or alkinyl, R<4> is hydrogen, a cyano group or halogen, R<5> is a cyano group or thiocarbamoyl, R<6> is one of the groups (1), (2), (3), wherein Q<1> and Q<2> are oxygen or sulphur, R<7> is hydrogen or optionally substituted alkyl, R<8> is hydrogen, a hydroxyl group, an amino group or optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonylamino, alkylsulfonylamino, alkenyl, alkenyloxy, alkinyl, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylcarbonylamino, cycloalkylsulfonylamino, aryl, aryloxy, arylamino, arylcarbonylamino, arylsulfonylamino, arylalkyl, arylalkoxy or arylalkylamino group, R<9> and R<10> are alkyl. A method for production of said compounds and their use as herbicides are described.

Description

Substituted phenyluracil

technical field

The present invention relates to novel substituted phenyluracils, processes for their preparation, and their use as herbicides.

Background technique

Some substituted uracils are known to have herbicidal properties (see DE 4131038, DE 4237920, DE 4329537, EP 408382/US 5084084/US 5127935/US 5154755, EP 542685, EP 563384, EP 648749, US 4979982, 0, US 0269781 WO 95/25725). However, these compounds have not gained any significant value statement so far.

Contents of the invention

其中R¹代表氢，卤素或任选被取代的烷基，R²代表任选被取代的烷基，R³代表氢，氨基或者代表烷基，链烯基或炔烃基，其各自任选被取代，R⁴代表氢，氰基或卤素，R⁵代表氰基或硫代氨基甲酰基，和R⁶代表下面的基团之一：

其中Q¹和Q²各自代表氧或硫，R⁷在每种情况下代表氢或任选被取代的烷基，R⁸代表氢，羟基，氨基或者代表烷基，烷氧基，烷基氨基，二烷基氨基，烷基羰基氨基，烷基磺酰基氨基，链烯基，链烯基氧基，炔烃基，环烷基，环烷基氧基，环烷基氨基，环烷基羰基氨基，环烷基磺酰基氨基，芳基，芳基氧基，芳基氨基，芳基羰基氨基，芳基磺酰基氨基，芳基烷基，芳基烷氧基，芳基烷基氨基，其中各基团任选被取代，并且R⁹和R¹⁰各自代表烷基。Therefore, the present invention provides novel substituted phenyluracils of general formula (I):

wherein R ¹ represents hydrogen, halogen or optionally substituted alkyl, R ² represents optionally substituted alkyl, R ³ represents hydrogen, amino or represents alkyl, alkenyl or alkynyl, each of which is optionally substituted Substitution, R ⁴ represents hydrogen, cyano or halogen, R ⁵ represents cyano or thiocarbamoyl, and R ⁶ represents one of the following groups:

wherein ^Q1 and ^Q2 each represent oxygen or sulfur, ^R7 represents hydrogen or optionally substituted alkyl in each case, ^R8 represents hydrogen, hydroxyl, amino or represents alkyl, alkoxy, alkylamino , Dialkylamino, Alkylcarbonylamino, Alkylsulfonylamino, Alkenyl, Alkenyloxy, Alkynyl, Cycloalkyl, Cycloalkyloxy, Cycloalkylamino, Cycloalkylcarbonylamino , cycloalkylsulfonylamino, aryl, aryloxy, arylamino, arylcarbonylamino, arylsulfonylamino, arylalkyl, arylalkoxy, arylalkylamino, each of which The group is optionally substituted, and R ⁹ and R ¹⁰ each represent an alkyl group.

其中R¹，R²，R³，R⁴，R⁵和R⁷各自如上定义，和R¹¹和R¹²各自代表氢，氰基，羧基或者代表各自任选被取代的烷基或烷氧羰基，或者(b)如果适当在稀释剂存在下和如果适当在反应助剂存在下，通式(Ia)羰基苯基尿嘧啶与通式(III)氨基化合物，或与式(III)化合物的酸加成物反应，其中R¹，R²，R³，R⁴，R⁵和R⁷各自如上定义，The new substituted phenyluracils of general formula (I) are obtained when carrying out the following reactions: (a) alkenes of general formula (II) if appropriate in the presence of diluents and if appropriate in the presence of reaction auxiliaries The reaction of phenyl uracil with ozone,

wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁷ are each as defined above, and R ¹¹ and R ¹² each represent hydrogen, cyano, carboxyl or represent each optionally substituted alkyl or alkoxycarbonyl , or (b) if appropriate in the presence of a diluent and if appropriate in the presence of a reaction aid, the carbonylphenyluracil of the general formula (Ia) with the amino compound of the general formula (III), or with the acid of the compound of the formula (III) adduct reaction, wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁷ are each as defined above,

其中R¹，R²，R³，R⁴，R⁵和R⁷各自如上定义，H ₂ NR ⁸ (III) wherein R ⁸ is as defined above, or (c) carbonylphenyluracil of general formula (Ia) with general formula (IVa) if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary or (IVb) alcohol and/or thiol reaction,

wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁷ are each as defined above,

HQ ¹ R ⁹ (IVa) HQ ² R ¹⁰ (IVb) wherein Q ¹ , Q ² , R ⁹ and R ¹⁰ are each as defined above.

The compounds of general formula (I) can also be converted into other compounds of general formula (I) according to the above definition using other conventional methods, for example by amination and/or alkylation (for example R ³ : H→NH ₂ , H→CH ₃ ), by reacting with hydrogen sulfide (eg R ⁵ : CN→CSNH ₂ ).

The novel substituted phenyluracils of general formula (I) have strong herbicidal activity.

In the above definitions, saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkyne groups, are in each case straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably represents fluorine, chlorine or bromine, especially represents fluorine or chlorine.

The present invention preferably provides the following compounds of formula (I), wherein R ¹ represents hydrogen, fluorine, chlorine, bromine or optionally fluorine- and/or chlorine-substituted C ₁ -C ₄ -alkyl, R ² represents optionally Fluoro- and/or chlorine-substituted C ₁ -C ₄ -alkyl, R ³ represents hydrogen, amino, represents optionally cyano-, fluorine-, chlorine- or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₆ -alkyl, or C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl optionally substituted by fluorine- and/or chlorine-, R ⁴ represents hydrogen, cyano , fluorine or chlorine, ^R represents cyano or thiocarbamoyl, and ^R represents one of the following groups: wherein ^Q1 and ^Q2 each represent oxygen or sulphur, R in ^each case represents hydrogen or represents _C1 - _C4 -alkyl optionally substituted by halogen- or _C1 - _C4 -alkoxy-, R ⁸ represents hydrogen, hydroxyl, amino, represents C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylamino, di-(C ₁ -C ₄ -alkyl )-amino, C ₁ -C ₄ -alkylcarbonylamino or C ₁ -C ₄ -alkylsulfonylamino, wherein each radical is optionally replaced by halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -Alkoxycarbonyl substituted, representing C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyl, wherein each group is optionally substituted by halogen, representing C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkyloxy, C ₃ -C ₆ -cycloalkylamino, C ₃ -C ₆ -cycloalkylcarbonylamino or C ₃ -C ₆ - Cycloalkylsulfonylamino, wherein each radical is optionally substituted by halogen or C ₁ -C ₄ -alkyl, or represents phenyl, phenoxy, phenylamino, phenylcarbonylamino, phenylsulfonylamino, Phenyl-C ₁ -C ₄ -alkyl, phenyl-C ₁ -C ₄ -alkoxy, phenyl- _{C 1} -C ₄ -alkylamino, wherein each group is optionally halogenated, C ₁ - C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -halogenated alkoxy substituted, and R ⁹ and R ¹⁰ each represent C ₁ -C ₄ - alkyl.

Detailed ways

其中Q¹和Q²各自代表氧或硫，R⁷在每种情况下代表氢或代表各自任选被氟，氯，甲氧基或乙氧基取代的甲基或乙基，R⁸代表氢，羟基，氨基，代表甲基，乙基，正-或异-丙基，正-、异-、仲或叔-丁基，甲氧基，乙氧基，正-或异-丙氧基，正-、异-、仲或叔-丁氧基，甲基氨基，乙基氨基，正-或异-丙基氨基，正-、异-、仲或叔-丁基氨基，二甲基氨基，乙酰基氨基，丙酰基氨基，正-或异-丁酰基氨基，甲基磺酰基氨基或乙基磺酰基氨基，其中各基团任选被氟，氯，甲氧基，乙氧基，甲氧羰基或乙氧羰基取代，代表丙烯基，丁烯基，丙烯基氧基，丁烯基氧基，丙炔基或丁炔基，其中各基团任选被氟，氯或溴取代，代表环戊基，环己基，环戊基氧基，环己基氧基，环戊基氨基，环己基氨基，环丙基羰基氨基，环丁基羰基氨基，环戊基羰基氨基，环己基羰基氨基，环丙基磺酰基氨基，环丁基磺酰基氨基，环戊基磺酰基氨基或环己基磺酰基氨基，其中各基团任选被氟，氯，溴，甲基或乙基取代，或者代表苯基，苯基氨基，苯基羰基氨基，苯基磺酰基氨基，苄基，苄基氧基或苄基氨基，其中各基团任选被氟，氯，溴，甲基，乙基，三氟甲基，甲氧基，乙氧基，二氟甲氧基或三氟甲氧基取代，和R⁹和R¹⁰各自代表甲基或乙基。The present invention particularly relates to the compound of formula (I), wherein ^R represents hydrogen, fluorine, chlorine, bromine or optionally fluorine- and/or chlorine-substituted methyl or ethyl, and ^R represents optionally fluorine- and /or chloro-substituted methyl or ethyl, ^R represents hydrogen, amino represents methyl, ethyl, n -, or iso-, propyl, n-, iso-, sec- or tert-butyl, or stands for propenyl, butenyl, propynyl or butynyl optionally fluoro- and/or chloro-substituted , R ⁴ represents hydrogen, fluorine or chlorine, R ⁵ represents cyano or thiocarbamoyl, and R ⁶ represents one of the following groups:

wherein ^Q1 and ^Q2 each represent oxygen or sulfur, ^R7 in each case represents hydrogen or represents a methyl or ethyl group each optionally substituted by fluorine, chlorine, methoxy or ethoxy, ^R8 represents hydrogen , hydroxy, amino, representing methyl, ethyl, n- or i-propyl, n-, i-, sec- or tert-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, sec- or tert-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, sec- or tert-butylamino, dimethylamino, Acetylamino, propionylamino, n- or iso-butyrylamino, methylsulfonylamino or ethylsulfonylamino, wherein each group is optionally replaced by fluorine, chlorine, methoxy, ethoxy, methoxy Carbonyl or ethoxycarbonyl substitution, representing propenyl, butenyl, propenyloxy, butenyloxy, propynyl or butynyl, where each group is optionally substituted by fluorine, chlorine or bromine, represents ring Pentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, cyclopentylamino, cyclohexylamino, cyclopropylcarbonylamino, cyclobutylcarbonylamino, cyclopentylcarbonylamino, cyclohexylcarbonylamino, cyclo Propylsulfonylamino, cyclobutylsulfonylamino, cyclopentylsulfonylamino or cyclohexylsulfonylamino, each of which is optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, or represents phenyl , phenylamino, phenylcarbonylamino, phenylsulfonylamino, benzyl, benzyloxy or benzylamino, wherein each group is optionally replaced by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl radical, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy, and ^R9 and ^R10 each represent methyl or ethyl.

The above general or preferred radical definitions apply to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. The definitions of these groups can be combined with each other as desired, ie, combinations between the indicated preferred ranges are included.

R⁶在这种情况下具有例如上面第1组中给出的意义。第4组 R⁶在这种情况下具有例如上面第1组中给出的意义。第5组 R⁶在这种情况下具有例如上面第1组中给出的意义。第6组 R⁶在这种情况下具有例如上面第1组中给出的意义。。第7组

R⁶在这种情况下具有例如上面第1组中给出的意义。第8组

R⁶在这种情况下具有例如上面第1组中给出的意义。第9组 R⁶在这种情况下具有例如上面第1组中给出的意义。第10组 R⁶在这种情况下具有例如上面第1组中给出的意义。第11组

R⁶在这种情况下具有例如上面第1组中给出的意义。第12组 R⁶在这种情况下具有例如上面第1组中给出的意义。第13组 R⁶在这种情况下具有例如上面第1组中给出的意义。第14组

R⁶在这种情况下具有例如上面第1组中给出的意义。第15组 R⁶在这种情况下具有例如上面第1组中给出的意义。第16组 R⁶在这种情况下具有例如上面第1组中给出的意义。第17组

R⁶在这种情况下具有例如上面第1组中给出的意义。第18组 R⁶在这种情况下具有例如上面第1组中给出的意义。第19组 R⁶在这种情况下具有例如上面第1组中给出的意义。第20组

R⁶在这种情况下具有例如上面第1组中给出的意义。第21组

R⁶在这种情况下具有例如上面第1组中给出的意义。第22组

R⁶在这种情况下具有例如上面第1组中给出的意义。Examples of compounds of formula (I) according to the invention are listed in the groups below. Group 1 ^R in this case has, for example, the definition given below: formyl, acetyl, methyliminomethyl, ethyliminoethyl, n-propyliminomethyl, isopropyliminomethyl , oximinomethyl, methoxyiminomethyl, ethoxyiminomethyl, n-propoxyiminomethyl, isopropoxyiminomethyl, n-butoxyiminomethyl, 1-methoxyiminomethyl -ethyl, methoxycarbonylmethoxyiminomethyl, ethoxycarbonylmethoxyiminomethyl, 1-methoxycarbonylmethoxyimino-ethyl, 1-ethoxycarbonylmethoxyimino-ethyl, 1,2-hydrazinoiminomethyl, methyl 1,2-hydrazinoiminomethyl, dimethyl 1,2-hydrazinoiminomethyl, acetyl 1,2-hydrazinoiminomethyl Iminomethyl, methylsulfonyl 1,2-hydrazinoiminomethyl, allyloxyiminomethyl, cyclopentyloxyiminomethyl, cyclohexyloxyiminomethyl, benzyloxyiminomethyl Aminomethyl, cyclopentyl 1,2-hydrazinoiminomethyl, cyclohexyl 1,2-hydrazinoiminomethyl, phenyl 1,2-hydrazinoiminomethyl, phenylcarbonyl 1,2-hydrazinoiminomethyl, phenylsulfonyl 1,2-hydrazinoiminomethyl, benzyl 1,2-hydrazinoiminomethyl, dimethoxymethyl, two Ethoxymethyl. Group 2 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 3

R ⁶ in this case has the meanings given, for example, for group 1 above. Group 4 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 5 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 6 R ⁶ in this case has the meanings given, for example, for group 1 above. . Group 7

R ⁶ in this case has the meanings given, for example, for group 1 above. Group 8

R ⁶ in this case has the meanings given, for example, for group 1 above. Group 9 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 10 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 11

R ⁶ in this case has the meanings given, for example, for group 1 above. Group 12 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 13 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 14

R ⁶ in this case has the meanings given, for example, for group 1 above. Group 15 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 16 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 17

R ⁶ in this case has the meanings given, for example, for group 1 above. Group 18 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 19 R ⁶ in this case has the meanings given, for example, for group 1 above. Group 20

R ⁶ in this case has the meanings given, for example, for group 1 above. Group 21

R ⁶ in this case has the meanings given, for example, for group 1 above. Group 22

R ⁶ in this case has the meanings given, for example, for group 1 above.

Using for example 1-[4-cyano-2-fluoro-5-(2-methoxycarbonyl-vinyl)-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl -4-trifluoromethyl-1 (2H)-pyrimidine and ozone are initiators, then the reaction process of the inventive method (a) can be illustrated by the following reaction formula:

Using for example 1-[4-cyano-2-fluoro-5-formyl-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1(2H)-pyrimidine and O-methyl-hydroxylamine are initiators, then the reaction process of the inventive method (b) can be illustrated by the following reaction formula:

Using for example 1-[4-cyano-2-fluoro-5-formyl-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl- 1(2H)-pyrimidine and methyl alcohol are initiators, then the reaction process of the inventive method (c) can be illustrated by the following reaction formula:

The formula (II) provides the general definition of the alkenylphenyluracils used as starting materials in the process (a) according to the invention for the preparation of the compounds of the general formula (I). In formula (II), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁷ each preferably or particularly have what has been indicated above, in relation to the description of the compounds of formula (I) prepared according to the present invention as preferred or particularly preferred definitions of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁷ ; R ¹¹ and R ¹² preferably represent cyano, carboxyl or C ₁ -C ₄ -alkoxycarbonyl .

The starting substances of the formula (II) have hitherto not been disclosed in the literature; as novel substances they constitute a subject of a prior art but not previously published application (cf. DE 19 528 186).

其中R¹，R²，R³，R⁴和R⁵各自如上定义，或式(V)化合物的酸加成物与碱金属亚硝酸盐或亚硝酸烷基酯，例如亚硝酸钠，亚硝酸钾，亚硝酸甲酯，亚硝酸正丁酯或叔丁酯，和与卤化氢(HX¹)，例如氯化氢或溴化氢，或者金属卤化物，例如氯化铜(I)或氯化铜(II)反应，并且，得到的通式(VI)重氮盐在卤化氢(HX¹)存在下，例如在氯化氢或溴化氢存在下，如果适当在水存在和如果适当在最初使用的有机溶剂的存在下，在0℃和50℃之间的温度下，与通式(VII)丙烯酸衍生物反应(接原文pp.18 其中R¹，R²，R³，R⁴和R⁵各自如上定义，X¹代表卤素，If appropriate in the presence of a diluent, such as water, acetic acid, acetonitrile and dichloromethane, at a temperature between -20°C and +10°C, when the aminophenyluracil of the general formula (V)

wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each as defined above, or the acid addition product of the compound of formula (V) with alkali metal nitrite or alkyl nitrite, such as sodium nitrite, nitrous acid Potassium, methyl nitrite, n- or tert-butyl nitrite, and hydrogen halides (HX ¹ ), such as hydrogen chloride or hydrogen bromide, or metal halides, such as copper(I) chloride or copper chloride ( II) reacting and, obtaining the diazonium salt of general formula (VI) in the presence of a hydrogen halide (HX ¹ ), for example in the presence of hydrogen chloride or hydrogen bromide, if appropriate in the presence of water and if appropriate in the organic solvent initially used In the presence of , at a temperature between 0°C and 50°C, react with acrylic acid derivatives of general formula (VII) (continued from the original text pp.18 wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each as defined above, X ¹ represents halogen,

R ⁷ CH=C(R ¹¹ , R ¹² ) (VII) wherein R ⁷ , R ¹¹ and R ¹² are each as defined above, and the resulting product is obtained in the presence of a diluent, for example in N,N-dimethylformamide Reaction with an acid acceptor such as sodium hydride in the presence of an acid acceptor at a temperature between 0° C. and 100° C. gives alkenylphenyluracils of general formula (II) (see Preparation Examples).

The formula (Ia) provides the general definition of the carbonylphenyluracils used as starting materials in the processes (b) and (c) according to the invention for the preparation of the compounds of the general formula (I). In formula (Ia), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁷ each preferably or particularly have what has been indicated above, in relation to the description of the compounds of formula (I) of the present invention, as Preferred or particularly preferred definitions of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁷ .

Formula (Ia) is a novel compound of the present invention; it can be prepared by process (a) of the present invention.

The formula (III) provides a general definition of the amino compounds which are also used as starting materials in the process (b) according to the invention for the preparation of the compounds of the formula (I). In formula (III), R ⁸ preferably or in particular has the definitions already indicated above as preferred or particularly preferred R ⁸ in relation to the description of the compounds of formula (I) according to the invention.

The starting materials of formula (III) are known chemicals for the synthesis.

The formulas (IVa) and (IVb) provide a general definition of the alcohols or thiols which are also used as starting materials in the process (c) according to the invention for the preparation of the compounds of the general formula (I). In formulas (IVa) and (IVb), each of Q ¹ , Q ² , R ⁹ and R ¹⁰ preferably or particularly has what has been indicated above, in relation to the description of the compounds of formula (I) of the present invention, as preferred Or particularly preferred definitions of Q ¹ , Q ² , R ⁹ and R ¹⁰ .

The starting materials of formula (IVa) and (IVb) are known chemicals for the synthesis.

Suitable diluents for carrying out the processes (a) to (c) according to the invention are in particular inert organic solvents. In particular include aliphatic, cycloaliphatic or aromatic optionally halogenated hydrocarbons, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, Chloroform, carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones such as acetone, butanone, or methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile or butyronitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-N - formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate; sulfoxides, such as dimethylsulfoxide; alcohols, such as methanol, ethanol, n- or iso-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether and their mixtures with water or pure water .

Process (a) according to the invention is carried out in the presence of reaction aids, preferred reaction aids being compounds with a reducing effect, for example zinc dust in acetic acid, hydrogen in the presence of palladium, sodium dithionite and dimethyl sulfide.

When carrying out the process (a) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, process (a) is carried out at a temperature between -100°C and +50°C, preferably between -80°C and +30°C.

Process (a) according to the invention is generally carried out at atmospheric pressure. However, it is also possible to carry out the process according to the invention under increased or reduced pressure—generally between 0.1 and 10 bar.

In a preferred embodiment of the process (a) according to the invention, the starting material of formula (II) is first added to the diluent and cooled to the desired temperature, and then ozone is introduced until the reaction is terminated. The cooling bath is removed, the reaction auxiliary is metered in, and the mixture is stirred at the desired temperature until the reaction is terminated. Workup is carried out by customary methods (see Preparation Examples).

Suitable reaction auxiliaries for process (b) according to the invention are generally customary inorganic or organic bases or acid acceptors. They preferably include alkaline earth or alkali metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as sodium, potassium or calcium acetate, lithium amide, sodium amide, Potassium Amide or Calcium Amide, Sodium Carbonate, Potassium Carbonate or Calcium Carbonate, Potassium Bicarbonate, Sodium Bicarbonate or Calcium Bicarbonate, Lithium Hydroxide, Sodium Hydroxide, Potassium Hydroxide or Calcium Hydroxide, Lithium Hydroxide, Sodium Hydroxide, Potassium Hydroxide or calcium hydroxide, sodium or potassium methoxide, sodium or potassium ethoxide, n- or sodium isopropoxide or n- or potassium isopropoxide, n-, iso-, sec- or t-butoxide sodium or n- , iso-, sec- or tert-butoxide; and basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N, -Dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N,-dimethylaniline, N,N,-dimethyl-benzylamine, pyridine, 2-methyl -, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl- Pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methylpiperidine, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1 , 5-diazabicyclo[4,3,0]-non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

When carrying out process (b) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, method (b) is carried out at a temperature between 0°C and 150°C, preferably between 10°C and 120°C.

Process (b) according to the invention is generally carried out at atmospheric pressure. However, it is also possible to carry out the process according to the invention under increased or reduced pressure—generally between 0.1 and 10 bar.

When carrying out the process (b) according to the invention, the starters are generally used in approximately equimolar amounts. However, it is also possible to use one of the starter components in a relatively large excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the desired temperature for several hours. Workup is carried out by customary methods (see Preparation Examples).

Process (c) according to the invention is preferably carried out in the presence of reaction auxiliaries, suitable reaction auxiliaries here being oxidizing agents, such as hydrogen peroxide, and acids, such as sulfuric acid.

When carrying out process (c) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, method (c) is carried out at a temperature between 0°C and 120°C, preferably between 10°C and 100°C.

Process (c) according to the invention is generally carried out at atmospheric pressure. However, it is also possible to carry out the process according to the invention under increased or reduced pressure—generally between 0.1 and 10 bar.

In a preferred embodiment of the process (c) according to the invention, a reaction auxiliary is added to the mixture of the starter of the formula (Ia) and the alcohol or thiol of the formula (IVa) or (IVb) and the mixture is stirred until the reaction is terminated. Workup is carried out by customary methods (see Preparation Examples).

The active compounds according to the invention can be used as defoliants, desiccants, straw killers and especially as weed killers. In a broad sense, so-called weeds are understood to be all plants that grow where they are not desired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amounts used.

The active compounds according to the invention can be used in connection with, for example, the following plants: Dicotyledonous weed species: Sinapis, Lepidium, Galium, Stellaria, Matricaria Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca ), Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Felicia (Carduus), Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Pona Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Cornflower Centaurea, Trifolium, Ranunculus and Taraxacum. Dicotyledonous crop species: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Flax ( Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis , and Cucurbita. Monocot weed species: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca ), Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monchoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, and Apera. Monocot crop species: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum (Panicum), Sugarcane (Saccharum), Pineapple (Ananas), Asparagus (Asparagus) and Allium (Allium).

However, the use of the active compounds according to the invention is by no means restricted to these species, but extends in the same way to other plants.

Depending on the concentration, the compounds according to the invention are suitable for the overall control of weeds, for example on industrial sites and on railways, roads or squares with or without trees. These compounds are also used to control weeds in perennial planting sites such as woods, ornamental trees, orchards, vineyards, lemon orchards, nut orchards, banana plantations, lawns, sports fields and pastures , coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantations and hop fields, and for selective control of weeds in annual plantation sites.

The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops by pre- and post-emergence methods.

The active compounds can be formulated into customary preparations, such as solutions, emulsions, wettable powders, suspensions, dusts, fine powders, pastes, soluble powders, granules, suspoe, and natural and synthetic materials impregnated with active compound materials, and microscopic capsules encapsulated in polymers.

These formulations can be produced in a known manner, for example, by mixing the active compounds with extenders, i.e. liquid solvents and/or solid carriers, and optionally using surfactants, i.e. emulsifiers and/or dispersants and/or effervescent agents. agent.

In the case of water as extender, it is also possible to use, for example, organic solvents as auxiliary solvents. Suitable liquid solvents mainly include: aromatic compounds, such as xylene, toluene or alkylnaphthalene, chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, vinyl chlorides or dichloromethane, aliphatic hydrocarbons, such as Cyclohexane or paraffins such as petroleum distillates, mineral and vegetable oils, alcohols such as butanol or ethylene glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone , strong polar solvents such as dimethylformamide and dimethylsulfoxide, and water.

Suitable solid carriers are: for example ammonium salts, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed Silica, alumina and silicates; suitable solid carriers for granules are, for example, crushed and broken natural minerals such as calcite, marble, pumice, sepiolite and dolomite, and organic and inorganic powders Synthetic granules, and granules of organic matter such as sawdust, coconut shells, corncobs and tobacco stems; suitable emulsifiers and/or foaming agents are, for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters , polyoxyethylene fatty alcohol ethers, for example, alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; suitable dispersants are: for example, wood elemental sulfurous acid waste liquid and methyl cellulose.

In formulations, binders such as carboxymethylcellulose and natural and synthetic polymers in powder, granular or latex form, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and egg Phospholipids, and synthetic phospholipids. Other additives may be mineral and vegetable oils.

It is also possible to use colorants, such as inorganic pigments, such as iron oxide, titanium oxide and Prussian blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as iron, manganese, boron, copper, Salts of cobalt, molybdenum and zinc.

In general, the preparations contain 0.1-95% by weight of active compound, preferably 0.5-90%.

For controlling weeds, the active compounds according to the invention can be used as such or in the form of their formulations or as mixtures with known herbicides, either as final formulations or as tank mixes.

Suitable for use in said mixtures are known herbicides, such as anilides, such as diflufenamide and propanil; aryl carboxylic acids, such as clopyralid, dicamba and picloram; aryloxy Alkanoic acids such as 2,4-D, 2,4-D butyric acid, 2,4-D propionic acid, fluroxypyr, 2-methyl-4-chloro, 2-methyl-4-chloropropionic acid and triclopyr; oxyphenoxyalkanoates such as dipropaprop, fenoxaprop, fluazifop, haloxyfop, and quizalofop; azinones such as dichlorpyr and pyridazol volts; carbamates, such as chlorphenamine, betaine, betainin, and aniline; chlorinated N-acetanilides, such as alachlor, acetochlor, butachlor, metazachlor, mesoprofen dinitroanilines, such as ansalin, pendimethalin, and trifluralin; diphenyl ethers, such as acifluorfen, carboxyfen, carboxyl Fluoxyfen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as chlormetron, diuron, fenuron, isoproturon, rituron, and methylbenzene Thiuron; Hydroxylamines, such as dipropazone, clethodim, diuron, sethoxydim, and oxaflume; imidazolinones, such as imazethapyr, imazethapyr, imazapyr, and imazaquin; Nitriles bromoxynil, dichnil, and ioxynil; oxyacetamides, such as mefenacet; sulfonylureas, such as amidosulfuron, benzsulfuron, chlorsulfuron, chlorsulfuron, ether yellow Trisulfuron, mesulfuron, nicosulfuron, flurizosulfuron, pyrazosulfuron, thiasulfuron, trisulfuron, and trisulfuron; thiocarbamates such as gramamon, mezat, Avename, Indalim, Dicamba, Tradamid, Procarbocarb, Methapen, and Avenfoam; Triazines, such as Atrazine, Cyanazine, Simazine, Siclozin, Terbuzin and terbutylazine; triazinones, such as hexazinone, fenmetrione, and metrizone; others, such as aminotriazoles, furazin, bentazone, cycloheptafen, clomazone, dichloro Picolinic acid, bisfenapyr, dithiopyr, efurazone, flurotrione, glufosinate-ammonium, glyphosate, isoxaben, pyridazat, quinclorac, quincetac, glufosin, and methion grass ring.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve the soil structure, are also possible.

The active compounds can be used as such or in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They can be used in a conventional manner, for example by watering, spraying, misting or spreading.

The active compounds according to the invention can be applied pre- or post-emergence of the plants. It can also be incorporated directly into the soil before sowing.

The amount of active compound employed can vary within a substantial range. This mainly depends on the nature of the desired effect. In general, the amount used is from 1 g to 10 kg of active compound per hectare of soil area, preferably from 5 g to 5 kg of active compound per hectare of soil area.

(方法(a))向已经冷却到-70℃的8.7g(22mmol)1-[4-氰基-2-氟-5-(2-甲氧羰基-乙烯基)-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和600ml二氯甲烷的混合物中通入臭氧45分钟。然后移去冷却浴，混合物与10ml二甲硫混合。一旦混合物温热至室温(大约20℃)，分离各相，有机相用水洗涤，硫酸钠干燥并过滤。用水泵抽真空来浓缩滤液，残余物溶解于乙醚，并且吸滤以分离结晶产物。The following examples illustrate the preparation and use of the active compounds of the invention. Preparation Example Example 1

(Method (a)) To 8.7 g (22 mmol) of 1-[4-cyano-2-fluoro-5-(2-methoxycarbonyl-vinyl)-phenyl]-3 which had been cooled to -70°C, Ozone was bubbled through a mixture of 6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine and 600 ml of dichloromethane for 45 minutes. The cooling bath was then removed and the mixture was admixed with 10 ml of dimethylsulfide. Once the mixture was warmed to room temperature (approximately 20°C), the phases were separated and the organic phase was washed with water, dried over sodium sulfate and filtered. The filtrate was concentrated with water pump vacuum, the residue was dissolved in diethyl ether and filtered with suction to isolate the crystalline product.

7.4 g (99% of theory) of 1-[4-cyano-2-fluoro-5-formyl-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl were obtained -4-Trifluoromethyl-1(2H)-pyrimidine, melting point 177°C. Example 2 (method (b))

At room temperature (about 20°C), 1.0 g (2.9 mmol) of 1-[4-cyano-2-fluoro-5-formyl-phenyl]-3,6-dihydro-2,6-dioxo -3-methyl-4-trifluoromethyl-1(2H)-pyrimidine, 0.25g (3.0mmol) O-methyl-hydroxylamine hydrochloride, a mixture of 0.25g (3.0mmol) sodium acetate and 20ml ethanol was stirred About 90 minutes. The mixture was then concentrated with water pump vacuum, and the residue was dissolved in water, mixed with 2N hydrochloric acid, and extracted with diethyl ether. The organic phase was dried over sodium sulfate and filtered. The solvent was then carefully distilled off from the filtrate by applying a water pump vacuum.

(方法(c))0.8 g (74% of theory) of 1-[4-cyano-2-fluoro-5-methoxyiminomethyl-phenyl]-3,6-dihydro-2,6-dioxo- 3-Methyl-4-trifluoromethyl-1(2H)-pyrimidine, melting point 80°C. Example 3

(method (c))

At about 10°C, mix 0.28g of hydrogen peroxide (30% concentration) and 0.59g of concentrated sulfuric acid, stir at about 20°C for about 2 hours, then add 1.0g (2.9mmol) of 1-[4-cyano- 2-fluoro-5-formyl-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine and 20ml of methanol In the mixture, the reaction mixture was stirred at room temperature (about 20° C.) for about 15 hours, and the crystalline product was isolated by suction filtration.

0.70 g (62% of theory) of 1-[4-cyano-2-fluoro-5-dimethoxymethyl-phenyl]-3,6-dihydro-2,6-dioxo- 3-Methyl-4-trifluoromethyl-1(2H)-pyrimidine, melting point 164°C.

表1：式(I)化合物的实施例

式(II)起始物： 实施例(II-1)

将1.8g(21mmol)丙烯酸甲酯，1.6g(15.5mmol)亚硝酸叔丁酯，1.6g(12mmol)氯化铜(II)和50ml乙腈的混合物冷却到大约0℃，并且在该温度下向其中滴加20ml乙腈中的3.3g(10mmol)1-(5-氨基-4-氰基-2-氟-苯基)-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶的溶液。然后使反应混合物温热至室温，并且在该温度下搅拌18小时。接着，加入20ml1N盐酸后，用乙酸乙酯萃取混合物，并用硫酸钠干燥有机相和过滤。浓缩滤液，并且残余物通过柱色谱处理。得到2.8g(理论量的65％)1-[4-氰基-2-氟-5-(2-氯-2-甲氧羰基-乙基)-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶，熔点46℃。Compounds of formula (I) such as listed in Table 1 below can also be prepared by the methods of Preparation Examples 1-3, and according to the general description of the preparation methods of the present invention.

Table 1: Examples of compounds of formula (I)

Formula (II) starting material: embodiment (II-1)

With 1.8g (21mmol) methyl acrylate, 1.6g (15.5mmol) tert-butyl nitrite, the mixture of 1.6g (12mmol) copper chloride (II) and 50ml acetonitrile is cooled to about 0 ℃, and at this temperature to Add dropwise 3.3g (10mmol) of 1-(5-amino-4-cyano-2-fluoro-phenyl)-3,6-dihydro-2,6-dioxo-3-methanol in 20ml of acetonitrile A solution of 4-trifluoromethyl-1(2H)-pyrimidine. The reaction mixture was then allowed to warm to room temperature and stirred at this temperature for 18 hours. Next, after adding 20 ml of 1N hydrochloric acid, the mixture was extracted with ethyl acetate, and the organic phase was dried over sodium sulfate and filtered. The filtrate was concentrated, and the residue was subjected to column chromatography. 2.8 g (65% of theory) of 1-[4-cyano-2-fluoro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl]-3,6-dihydro- 2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine, melting point 46°C.

To 2.0 g (4.6 mmol) of 1-[4-cyano-2-fluoro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl]-3 which had been cooled to 0°C under stirring, 6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H)-pyrimidine and 30ml of N, N-dimethylformamide mixture was added 0.22g of sodium hydride ( 60% strength), the reaction mixture was first stirred at 0° C. for 15 minutes, then at 20° C. for about 60 minutes, and finally at 60° C. for 6 hours. The mixture was then concentrated in a water pump vacuum, the residue was stirred with diisopropyl ether, and the crystalline product was isolated by suction filtration. 1.1 g (60% of theory) of 1-[4-cyano-2-fluoro-5-(2-methoxycarbonyl-vinyl)-phenyl]-3,6-dihydro-2,6- Dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine, melting point 154°C. Formula (V) starting material embodiment (V-1)

Add to 0.50g (1.2mmol) 1-[4-cyano-2-fluoro-5-trifluoroacetylamino-phenyl]-3,6-dihydro-2,6-dioxo-3- Add 0.17g (1.2mmol) pivaloyl chloride to the mixture of methyl-4-trifluoromethyl-1(2H)-pyrimidine, 1ml triethylamine and 50ml acetonitrile, the reaction mixture was stirred at 20°C for 18 hours, and then Stir at 60°C for 15 hours. The mixture is then concentrated in water pump vacuum, the residue is shaken with 1N hydrochloric acid/ethyl acetate, the organic phase is separated, dried over sodium sulfate and filtered. The filtrate was concentrated under water pump vacuum and the residue was subjected to column chromatography (silica gel, chloroform/ethyl acetate, 1:1 by volume).

In addition to unreacted 1-[4-cyano-2-fluoro-5-trifluoroacetylamino-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4- Trifluoromethyl-1(2H)-pyrimidine (first fraction: 0.30 g), yielding as second fraction 0.2 g (50% of theory) of 1-[4-cyano-2-fluoro-5 -Amino-phenyl]-3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidine, melting point 195°C. Application Example Example A Pre-emergent test solvent: 5 parts by weight acetone emulsifier: 1 part by weight alkyl aryl polyglycol ether

To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added, and the emulsifiable concentrate is diluted with water to the required concentration.

Sow the seeds of the test plants in normal soil. After 24 hours, the soil is sprayed with the preparation of active compound. Advantageously, the amount of water used per unit area remains constant. The concentration of active compound in the formulation is not critical, only the amount of active compound applied per unit area is important.

After three weeks, the extent of plant kill was determined as percent kill compared to growth of untreated controls. the data shows:

0% = no effect (like untreated control)

100% = complete destruction In this test, when applied at a rate between 30-125 g/ha, for example the compounds of Preparation Examples 1, 2 and 4 show very strong weed control such as Amaranthus ( 95%), Sinapis (100%), Xanthium (100%), Digitaria (80-100%), Setaria (95-100%), Herbicidal activity of Chenopodium (100%), Matricaria (100%), and Veronica (100%), and crops such as corn, barley, and cotton have good tolerance to them Receptivity (0-30%). Experiment solvent after embodiment B bud: 5 parts by weight acetone emulsifier: 1 part by weight alkyl aryl polyglycol ether

To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added, and the emulsifiable concentrate is diluted with water to the required concentration.

Test plants 5-15 cm high are sprayed with the preparation of active compound in such a way that the specifically desired amount of active compound is applied per unit area. The concentration of the spray liquor is chosen such that the specifically desired amount of active compound is applied in 1000 L of water/ha.

After three weeks, the extent of plant kill was determined as percent kill compared to growth of untreated controls. the data shows:

0% = no effect (like untreated control)

100% = complete destruction In this test, when applied at a rate between 30-125 g/ha, for example the compounds of Preparation Examples 1, 2 and 4 show very strong weed control such as Abutilon (100%), Amaranthus (100%), Galium (100%), Datura (100%), Polygonum (100%) and Solanum Solanum (100%), and crops such as wheat tolerated some of them well (10%).

Claims (6)

1. the phenyl uracils that replaces of general formula (I): Be characterised in that R ¹Represent hydrogen, R ²The C that representative is replaced by fluorine _1-4Alkyl, R ³Represent C _1-6Alkyl, R ⁴Represent halogen, R ⁵Represent cyano group, R ⁶One of group below the representative:

Q wherein ¹And Q ²Represent oxygen separately, R ⁷Represent hydrogen in each case, R ⁸Represent C _1-6-alkoxyl group, two (C _1-4-alkyl)-and amino, R ⁹And R ¹⁰Represent C separately _1-4Alkyl.

2. the phenyl uracils of the replacement of the general formula of claim 1 (I) is characterised in that R ²Represent CF ₃, R ³Represent CH ₃, R ⁴Represent F, R ⁸Representative-OCH ₃,-N (CH ₃) ₂, R ⁹And R ¹⁰Represent CH separately ₃

3. the preparation method of the phenyl uracils of the replacement of the general formula of claim 1 (I) is characterised in that the alkenyl phenyl uracils of (a) general formula (II)

R wherein ¹, R ², R ³, R ⁴, R ⁵And R ⁷As above definition, and R separately ¹¹And R ¹²Represent hydrogen separately, cyano group, optional separately substituted alkyl of carboxyl or representative or carbalkoxy, with ozone reaction, the perhaps carbonyl phenyl uridylic of (b) general formula (Ia) R wherein ¹, R ², R ³, R ⁴, R ⁵And R ⁷As above definition separately, with the aminocompound reaction of general formula (III),

H ₂N-R ⁸(III) R wherein ⁸As above definition, perhaps the sour affixture with formula (III) compound reacts, perhaps the carbonyl phenyl uridylic of (c) general formula (Ia)

R wherein ¹, R ², R ³, R ⁴, R ⁵And R ⁷As above definition separately, with general formula (IVa) or (IVb) alcohol and/or thiol reactant,

HQ ¹R ⁹(IVa) HQ ²R ¹⁰(IVb) Q wherein ¹, Q ², R ⁹And R ¹⁰As above definition separately.

4. herbicidal composition is characterised in that, it contains the phenyl uracils of the formula (I) of at least a claim 1.

5. control is not expected to be characterised in that the method for plant, the phenyl uracils of the general formula (I) of claim 1 is acted on do not expect plant and/or its growth region.

6. the purposes of plant is not expected in the control of the phenyl uracils of the general formula of claim 1 (I).